In an attempt to have a little fun with ALL of the characters rather than just TFW, I am announcing my 20 Different Pairings Challenge!
How It Works:
I have created a list of 20 different pairings with lots of different characters! Starting next week, I will release a smutty one shot for each pairing! (Note: This is not an ongoing series, as each one shot will be a stand alone piece.) I get to challenge myself to write new characters, and you get some new and different smut. EVERYONE WINS.
Here’s The List:
1. Dean x reader 2. Sam x reader 3. Cas x reader 4. Crowley x reader 5. Dean x Jo x reader 6. John x reader 7. Charlie x reader 8. Benny x reader 9. Sam x Jody x reader 10. Lucifer x reader 11. Cas x Meg x reader 12. Rowena x reader 13. Dean x Sam x reader 14. Cain x reader 15. Dean x Benny x reader 16. Gabriel x reader 17. Sam x Ruby x reader 18. Dean x Donna x reader 19. Rowena x Lucifer x reader 20. Cas x Dean x reader
Here’s YOUR Job:
Send me your kinks! Have a particular kink you’d like to see with a specific character? Tell me! Have an idea for a smutty one shot that you’ve been thinking about? Send it!
BUT PLEASE FOLLOW THESE RULES:
Tell me the number of the pairing you are requesting for, then your kink. So, for example, let’s say I really wanted a Crowley fic that includes breath play. I would send an ask that says “Number 4, breath play”. PLEASE DO NOT REQUEST OTHER ONE SHOTS AT THIS TIME.
I will choose the ones I will write, then create a masterlist of the prompts on Sunday, so that you know what’s coming in advance! (Please don’t be offended if I don’t choose yours, I promise it isn’t personal!)
I can’t wait to write all of these smutty kinks for y’all!!
Summary: Y/N is happy with being the nobody in her daily life. From school to at home, she’s always been the misfit. Dean is a popular football player who is more focused on keeping his parents happy than himself. Meeting Y/N makes Dean see things in a different light. One night with the misfit girl and Dean’s hooked.
High school was hard for you. School in
general always had been. Your older sister had graduated with honours
and was gone off to University to become some big shot Lawyer. You
were in your last year and honestly could not wait to get out of the
shit hole of a school that you had been stuck in for three years now.
In English class you sat and stared out
the window. Surprisingly English was one of your favourite classes.
You thought Shakespeare and novels like Lord Of The Flies and The
Catcher in the Rye were far more important to your life than
Mathematics quadratic formula’s and algebraic equations. Still, this
class you just couldn’t focus. It was last period and you were
jonesing for a cigarette already.
Unfortunately the cigarette habit came
hand in hand with the misfit label. That’s what you were. A nomad.
You hated school. Hated your parents. Hated the law. You had a few
friends who also fell under the misfit category. You didn’t have good
grades and you were always living in your sisters larger than life
shadow. What else would you be.
But you liked being a nomad. A nobody.
You weren’t smart enough to be a nerd who got picked on. You didn’t
wear crazy clothes and go looking for attention so that you could get
called names. You kept to yourself and no one ever noticed you. And
you wanted to keep it that way.
People actually liked you even if you
didn’t like them. You could buy cigarettes so a lot of the
cheerleaders and jocks who smoked casually on weekends or at parties
came to you to get them for them, afraid if they got caught that the
school would kick them off their sport teams or something. Sometimes
you got invited to their parties, but you never showed up.
The bell rang and snapped you out of
your trance. You quickly got your stuff together and headed out of
the class and down the hall. The fresh free air hit your face and you
felt like you had just got out of prison after years of being locked
behind bars. You pulled out a cigarette and lit it as you headed to
your car. The smoke you blew out quickly disappeared as you walked
across the parking lot. That’s when Benny came up to you.
“You coming tonight?” he asked,
grabbing your cigarette from you and taking a draw. You rolled your
eyes and let it happen.
“Yeah, I’m coming. I’m not missing
this one because my parents are dicks. I swear one of these days I’m
getting emancipated.” you let out. Benny chuckled and passed your
cigarette back to you before reaching your car.
“Alright darlin’. I’m counting on you
being there, you’re our best you know.” you grinned and reached up
to give Benny a kiss on the cheek.
“I know.” you said with a cocky
smirk. Benny rolled his eyes and opened your door to your car for
“Eight o'clock sharp. You know the
spot, don’t be late.” Benny demanded. You smiled and nodded and he
closed your door before you drove off.
You decided to leave your house at
seven to give yourself some time just in case anything went wrong.
You put on a oversized grey sweater and black leggings. Over the
sweater you wore a leather jacket that matched your black combat
boots. To top that all off you wore a black beanie. You always
dressed dark which was how you liked your make up too. The only bit
of colour you had on was the deep red lip stick you wore on your
You packed up your backpack and made
sure you had your bottle of Vodka stuffed in there too. You weren’t
risking getting caught by your parents this time so you climbed out
your window and onto the roof. It was a long way down to the ground
so you had to strategically climb down a tree close to the house.
Once you got down and into your car, starting it up without them
noticing was the issue. But you had a plan in place.
Your neighbour Bobby Singer had always
been like a cool Uncle to you. Your parents thought of him as just an
old drunk but you thought he was great guy. He got you more than they
ever did. He helped you sneak out from time to time too.
“Put her in drive kid and I’ll start
pushing.” Bobby called out in a whisper. You did so and the car
started rolling down the road until it was at a safe distance that
you could start it without your parents hearing.
“Thanks Bobby!” you called out as
he walked back down the road.
“Don’t mention it kid! It’s a Friday
night, your parents need to get the sticks out of their asses.” he
exclaimed. You laughed and nodded your head.
“Tell them that!” you chuckled
before driving off. You got about fifteen minutes away from your
house when your car decided to give out. Opening up the hood smoke
came bellowing out. “Fuck!” you exclaimed and looked down at your
watch. It was seven twenty eight. By now everyone was probably there,
your phone was dead so you couldn’t call a tow or a ride, and you
were on a back road with barely any traffic and it was getting dark.
You were basically screwed. Benny was
going to kick your ass. Your parents were going to kick your ass. You
had nothing better to do than sit on the trunk and drink your Vodka.
After a couple swigs you felt a little buzz coming on. At the same
time you saw a pair of headlights coming your way. You jumped down
off of the hood and waved them down. Once they got closer you
recognized the jet black Impala. It was the beautiful car that
belonged to Dean Winchester.
The roar of his engine died down and he
climbed out of the car. The first thing you noticed was his emerald
eyes that were flickering up and down as he scanned over you. You
felt a little nervous under his glare, like he was judging you or
“Hey. Thanks for stopping.” you let
out, breaking the silence.
“Yeah no problem. What happened?”
Dean asked. His eyes quickly left yours and looked down at the bottle
of Vodka in your hand. He furrowed his brows when you brought the
bottle to your lips. After taking a swig you closed it and put it in
“Don’t worry. I didn’t start drinking
it until after the car died.” you chuckled. Your mind was a little
hazed now and you felt a little to confident at this point. “Do you
know much about cars?” you asked.
“Yeah actually, I do.” he replied,
walking over to the front of the car. You followed behind and watched
as he studied the engine. Dean shook his Letterman jacket off,
exposing his muscular arms. You couldn’t help but stare. Normally
this didn’t phase you but right now, while he was knelt over the car
examining the engine, Dean looked rather sexy.
Dean Winchester was football player for
the school team. He wasn’t captain or anything but he was pretty
popular. Everyone liked him, even the misfits like you. He was just a
nice guy who got along with most everyone.
“You blew a gasket.” Dean spoke up,
snapping you out of your trance.
“Can you fix it?” you asked.
“Not here. But I’ll tell you what, if
you can get me cigarettes for free for a month, I’ll get it towed to
my house in the morning and I’ll fix it there. No charge. It’s a good
deal.” he smiled. You gave him a questionable look for a second but
that quickly turned into a smile.
“Deal. But you have to give me a
ride.” you exclaimed. Dean put out a hand to close the deal. You
shook and then made your way over to his car. When you got in you
noticed the smell of cigarettes which was kind of comforting. You had
sold to Dean for a while now but it was obvious that most of the
smokes were smoked in this vehicle.
“Home?” he asked. You quickly shook
your head no.
“Oh no. Hell no. I’m not going home
tonight.” you replied. Dean gave you a puzzled look.
“Why not?” he questioned as he lit
up a cigarette and handed to you. You gladly took it.
“First of all, my parents don’t even
know I’m out. Second, if they find out I was out and my car broke
down, they will kill me. Third I have somewhere that I have to be and
if I’m not there in fifteen minutes, I’m toast.” you explained.
Dean nodded and looked at the clock.
“Where do you need to be?” Dean
asked. You took a draw and blew out smoke.
“Downtown, harbour side. It takes
exactly fifteen minutes to get there from here.” You let out.
“I’ll get you there in ten.” Dean
said, and with that his tires spun in the dirt and you were off.
Ten minutes later, just as he had
promised, you and Dean pulled up to an abandoned warehouse. Dean
looked at the place and furrowed his brows.
“This is where you need to be so
badly?” he questioned. You nodded and pointed at a parking lot down
by the boats that had a few cars.
“Park there, it’s less suspicious.”
“Why am I parking?” Dean asked as
he pulled into a parking spot.
“Aren’t you a little curious as to
what we’re doing out here?” you said, taking another swig of Vodka
before putting the bottle away.
“Well yeah but-” Dean started but
you cut him off.
“Well c'mon then, I’ll show you.”
you got out of the car and hauled your backpack over your shoulder.
Dean was hesitant but he got out and followed behind you.
As you approached the warehouse you
slipped in through a loose fence board that lead down an ally on the
side. Dean nervously followed and you could tell he’d never done
anything like this before. When you got to the end of the ally, it
opened up into another larger ally at the back of the rows of
buildings. Benny, Ruby, Meg, and Gabe were sat around waiting for you
to show up.
“I told you I’d be here.” you said,
playfully punching his arm as you walked by him. Dean appeared from
the ally and everyone’s eyes landed on him.
“What’s he doing here?” Meg asked.
“Winchester? He’s cool guys. If not
for him, I wouldn’t be here.” you laughed. “The shit box broke
down once again.” Everyone let out a chuckle and Benny put out a
hand to Dean.
“If you’re cool with the kid, you’re
cool with us brother.” Benny let out. Dean smiled and took his
hand. He looked around at his surroundings. There was nothing but
“What are you guys doing anyways?”
he asked. You smiled and handed him the bottle of Vodka. He took a
small swig and grimaced. He was always more of a whiskey man.
“You’ll see.” Ruby said. “You go
first Y/N.” you nodded and took out your spray paint. Dean quickly
realized what was going on and his mouth hung open a little.
“You’re vandalizing?” he said with
a harsh tone. You started anyways.
“We are making ark work. It’s
different. We’re not writing curse words on brick walls. It’s real
art.” you explained.
“It’s also illegal.” Dean
“And drinking and driving isn’t?”
you said gesturing to the bottle of Vodka in his hand. Dean thought
about it for a minute. He never got to do stuff like this. His
parents expected so much from him that he never broke the rules just
to keep them happy. It was time to be a little reckless. He took
another swig of Vodka.
“Touche.” Dean relaxed and sat back
with Benny and the others, watching you work. He liked how happy you
looked doing it. The way your tongue stuck out when you were trying
to focus on one thing. You looked so care free. He wished he had
something like that. Football was it for him and he didn’t even like
it all that much.
After an hour you finished up the
painting and stepped back to admire your work. Dean and the others
had just about finished off the bottle of Vodka but left the last bit
for you. You took it and downed the rest, felling satisfied with the
buzz you had. Everyone looked up at the art work you had just placed
on the wall.
“I think this is your best yet.”
Benny said patting you on the back. You smiled and sat back next to
Dean as the others grabbed there cans and started making their
“What do you think now?” you asked
Dean. “Still vandalism?” Dean shook his head.
“You’re really good. It’s beautiful.”
Dean said admiring your work. You had painted a girls face on the
wall. Her hair was all messy and falling everywhere and her eyes were
wide. Over her mouth were two pieces of duck tape and on her wrists
which were up by her face she wore hand cuffs. It was all done in
black and white with a little blue here and there. “Why this?”
“What do you mean?” you asked.
“The duck tape. The handcuffs? What
does it mean?” Dean replied.
“I don’t know…It’s just
sometimes… sometimes I feel like this. A prisoner I guess.” you
said with a sigh, staring down at your feet in front of you. Dean
smiled. He got it. He felt the same way.
“Me too… I mean I know it seems
like I have everything figured out and everything I ever wanted. But
I don’t… I have everything everyone else wants me to have.” Dean
let out. You looked over at him, your eyes searching his for some
sort of lie. But he was telling the truth.
“You know, you don’t have to be
perfect for anyone. You can say no to people. I did. My parents hate
me and my marks suck and I’m probably going no where, but I’m happy.”
you smiled over at Dean. Dean smiled back but this time his eyes
couldn’t leave yours.
He was drawn to you for some reason. It
might have just been the booze and the way that your hair was falling
around your shoulders and the way you lips were curved into this
perfect smile. What ever it was, in that moment he wished things were
different. If they were than maybe he’d kiss you right now.
You felt Dean’s gaze burn into. You
wanted to inch closer to him but something in you stopped yourself.
Instead you settled for his fingers tangling in yours casually. You
both kept your gazes on each other for a while. Until you saw a flash
of blue and red lights behind Dean. You looked up to see a cop car at
the end of the ally.
“Shit! Benny, we got company.” you
said, getting up from the ground with the help of Dean. You could see
the panic on Dean’s face.
“I-I can’t get busted for this.” he
exclaimed. You grabbed his hand and tried to calm him down.
“Don’t worry, we have a plan.” you
“Yeah, everyone split up. We meet at
58, got it?” Benny said. Everyone nodded and ran in opposite
directions. You and Dean headed for a small ally on the other side
that lead up to a small street.
“You go first.” Dean said as you
came upon a fence blocking your way. You could see the cop coming for
you now and closing in.
“No, you go. If you get caught that’s
the end of football and your parents will kill you.” you explained.
“I get caught and it’s just another day of the year… well sort
“I can’t let you do that for me Y/N.”
Dean said. The cop was getting closer and there wasn’t much time.
“Yes you can! Now go. 58 Blackwood
Street. They’ll be there.” you told Dean. Dean and you shared a
glance and he was hesitant on leaving you. “Go.” you shouted. He
climbed the fence and got to the other side. Looking back he saw the
cops hand land on your shoulder. He decided to run. You wanted him to
You looked the officer straight in the
eye and smiled. “Heya Jody! How’s it going?”
“Alright Y/N. Cut the bull shit,
where are your friends?” Jody Mills, the Sheriff asked.
“I’ll never tell you.” you shouted
“Tell me or you’re going to the
station.” Jody demanded.
“Jody, you know I’m never going to
break. Haven’t we done this enough for you to know that I’m no rat.”
you smirked. Jody shook her head and took you by the arm.
“The station it is then.” the
Sheriff said, guiding you to the car.
Dean ran and ran until he made it to 58
Blackwood. He was alone for a few minutes and then one by one Benny
and the others showed up, all out of breath. They all started looking
“Where’s the kid?” Benny asked
“She got caught. She wanted me to go
so I didn’t get in shit.” Dean said, still out of breath.
“You let her get caught!” Meg
shouted. Dean looked down at the ground feeling more guilty than
“Hey, it ain’t his fault. She brought
him and he was her responsibility. Plus the kid is always fine.”
Benny chuckled. The group all laughed a little and Dean lightened up.
“How are we getting home?” Gabe
“My car is down by the harbour. I
didn’t have that much to drink and that run sobered me up mostly, I
can drive you all home.” Dean let out. They all nodded and when
they felt it was safe, made their way back down to the harbour.
Dean wondered if he’d see you tomorrow.
How mad would your parents be? He wanted to see you. He never wanted
to stop seeing you. At the beginning of the night he barely knew you,
and now it felt like he’d known you all his life. You made him feel
like he could be himself and not the person everyone wanted him to
be. It was like when he was with you, the weight on his shoulders was
gone. He felt free. He was falling for you and didn’t even really
know it yet.
The thing Meg misses the most about Earth are the magazines: she could spend hours just flipping through the pages filled with cheap gossips about celebrities, dieting tips, fashion and crap like that.
She loved those things: but Benny makes up for the lack of them. He’s an amazing storyteller: she’s older than him, but doesn’t have his gift for stories, his ability to make you feel like you’re in it, like you’re living it first hand.
Meg looks at his with a soft smile lighting her face, while he goes on telling her about his granpa Winston and his crazy adventures: she knows it’s almost all bullshit, but hey, they’re in Purgatory, they have to find ways to spend the time they don’t occupy chopping monsters heads off.
“And so he finally reached the other shore and found this gorgeous woman waitin’ for him, with nothing but her long hair as a cover.”
“You’re such a liar.”
Benny looks offended for a second, then laughs.
“Ain’t that so…”
“But you’re a good liar.”
Meg settles in his lap and Benny’s arms circle her, holding her tight, but gently, like he always does.